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Halloween…a long time ago
Halloween…1991 I was still married and still very new to crossdressing
when this occurred, with very little bisexual experience
also.
My wife and I were asked to attend a Halloween party with
some friends at the local VFW, the same one we attended the
year before and won first place for most original costume,
which I had chosen. I went as the Pope and she was the devil.
She asked me to pick this years theme since I was always more
creative than her and had such great success the previous
year, and since I had gotten more into my crossdressing, I wanted to go as a woman….naturally.
My wife was very unsupportive of my desire to dress and reluctant
to this, but then I suggested that I go as a hooker and she can go as my pimp. She was still reluctant
until she saw these shoes at a thrift store that were perfect for
her costume, they were red and black wingtips. She then
found a gawdy purple mens suit at a thrift store and we decided to go as I suggested.
i wore a skin tight blue mini skirt and a top that tied in front
just under where my boobs would be. Finished it off with
makeup and bright red glossy lipstick. I shaved every inch
of my body, which I do anyway, paying particular attention
to my chest and stomach since they would be very visible
with this costume.I also wore lace top thigh highs with
garter and the straps were clearly visible at the bottom
of my short skirt, and a new pair of 5 inch spike heels.I then spritzed
some sexy perfume all over and My costume was complete.
We got to the party and sat with her sister and husband, and
just drank and danced and talked. I got up every chance I
could since I loved hearing my heels click on the tile floor,
it just completed me. Finally I had to pee and went to the
restroom, there I stood in front of the 2 doors, choosing
which one to enter. If I was in a club, it wouldve been the
ladies room, but since this was a str8 venue, I went into
the mens. I was alone as I entered the booth and did my business.
I stopped to wash up and re-apply my lipstick and perfume,
and this guy that had been sitting at the table next to us
came in. He made small talk as he stood at the urinal and when
he was done, he stood next to me at the mirror as I finished
my lips. He commented that I looked really good, it was a
great costume, and I made it look good….Hell, he said,
you look better than some of the real women out there…..I
smiled and thanked him and thought nothing of it as I went
back to my seat. i did some dancing with my wife and was beginning
to sweat after awhile. the heat was on and with a wig and heavy
makeup, it was very hot. I told my wife that I was going outside
to smoke and get some fresh air. She came with me, and we stood
out in the chilly air with some other people, including
the guy from the mens room, who I noticed couldnt keep his
eyes off of me. I was flattered. We went back in for more drinks and dancing, and after a bit I saw my male admirer make a motion
that he wanted to go out for a cigarette and motioned for
me to come along. I told the wife I was going out for more fresh
air as she danced with her sister.
This guy and me were the
only ones out there this time and he lit my cigarette for
me, just like a gentleman. He complimented me on my sexy
legs and my sexy appearance and jokingly asked if I was ready
to turn any tricks, seeing as I was playing the part of a hooker.
I just laughed and said no, its just a costume. He then said,
“its more than just a costume isnt it?” I was
stunned at this comment, not offended, just stunned that
it appears I had been found out. I just smiled in reply. He
then put a hand on my ass cheek and asked if I shaved my legs
for tonight, and I replied that I had. He then asked if I shaved
anywhere else…..as I was about to reply, another couple
came outside for air. He moved towards the parking lot around
the side of the building and when he was out of sight of the
others, he motioned for me to follow him. My heels clicked
on the pavement as I walked to follow him. We weaved thru
the parked cars and finally stopped near the end of the parking
lot, next to what turned out to be his car. He began with,
” you didnt have the chance to answer my question”.
I smiled and said “all over”. “So it is
more than just a costume isnt it Lisa?” I smiled and
flirtingly said, “maybe”. He said that he was
really attracted to ladies such as myself, and then he leaned
in and kissed me on the lips. I was shocked, after all, I had
sucked the other cd girl just over a month ago, and then last
month had done like 4 or 5 guys at the gloryhole, but had never
been kissed on the lips while dressed like this, especially
by a man. I stood there stunned, unable to speak or know what
to do as he rubbed my legs and played with my ass. He squeezed
my ass again and leaned in and kissed me again, shoving his
tongue in my mouth and I found myself kissing him back, and
getting aroused. He then took my hand and placed it on his
crotch, he was rock hard and I felt it and squeezed it and
wanted to see it.
Lets sit in the car he suggested, and I slid
into the passenger seat, and we made out like 2 teenagers
as I stroked his now bare cock. He was dripping with pleasure
and I wanted to taste that pre cum, it is sooooo sweet, so
I leaned over and took him in my mouth, and did what I had learned
to do so good. He gave me a nice reward, and we sat up and cleaned
up and talked awhile, me telling him how new I was to this.
And him telling me how good I was and that he’d like to
see me again, that we can get a room sometime. I said it would
be nice and he gave me his phone #. Be discreet he said and
I assured him I would. i did see him a few more times over the
months that followed and then he moved away to the west coast.
My makeup and lips were a mess and I freshened up as best as
I could before going back in the building. We got stares
from the people that were gathered outside as we entered,
but I didnt care. I found my wife and she said I was gone a long
time, I just told her I was talking.
We all went out to a diner
after the party was over, and the door was held for me by a
foreign looking man as I entered, and it felt good to think
that maybe he thought I was a real woman. I turned and in my
deepest male voice thanked him, and had a good laugh about
it afterwards. i could still taste the cum in my mouth as
I drank my coffee and ate a meal. My new friend winked at me
and I just smiled as we drove off and headed home.
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